


Reckless Hearts // a "Gossip Girl" Next Generation Story

by Starcrossedjedis



Category: Gossip Girl
Genre: Annie Montgomery FC - Jessica Stroup, Celeste Kingston FC - Bella Thorne, F/M, Gen, Jay Tyler FC - Blair Redford, New names old drama, Other, Quinn Davenport FC - Jacob Elordi, gossip girl 2018, social media be a bitch, we all know we would've loved Gossip Girl to run a Twitter
Language: English
Status: In-Progress
Published: 2018-06-11
Updated: 2018-08-10
Packaged: 2019-05-21 04:32:58
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 8,168
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14908395
Author URL: https://archiveofourown.org/users/Starcrossedjedis/pseuds/Starcrossedjedis
Summary: “Hey... You probably won't even listen to this, but I- I don't know... I guess I just wanna apologize. For showing up at your place like this. For trying to make you talk even though you said you weren't ready. But the thing is, Annie, I am ready to talk about this. I have been ready to talk about this for over a month now. And I know you feel guilty, Annie. I'm feeling guilty, too. But we can't just ignore what happened. Annie, we slept together and all the silence in the world isn't going to undo that...”





	1. pt. 1

**Author's Note:**

> This is an OC driven Next Generation Gossip Girl story. This story is a way for me to try a few of my 'original' ideas in the relative safety of someone else's sandbox. I hope you enjoy reading this half as much as I'm enjoying writing it.  
> -XOXO-

 

 

~*~

 

**Hello, Upper East Siders,**

did you miss me?

I know, it's been a long, quiet summer, but things are about to get exciting. Dust off those party dresses, because it looks like our Queen and her favorite Lady have finally pulled up stakes in St. Barts and are on their way to spice up life in the Hamptons just in time for Jack Bass's annual Fourth of July party.

We're all left to guess what this means for our very own Royal Couple. Prince Charming seemed unusually reclusive these past few weeks – is this thunder I hear rolling up on Royal Cloud Nine or are we in for a reunion worthy of a fairy tale?

And what about fair Lady Anne?

Rumor has it she's been rejecting an awful lot of calls on her Caribbean getaway. Does this mean there's finally a suitor somewhere waiting for her to answer his desperate courtship?

I think it's about damn time! After all, she can't play the Royal Third Wheel forever. It's safe to assume that Queen C has no intention of sharing her prom date for yet another year. Not when this time there's The Crown at stake.

It's the Fourth of July, bitches. And this girl right here's expecting some fireworks.

This hot summer just got even hotter.

**-XOXO- Gossip Girl**

 

 

~*~

 

 

“I hate this fucking hellsite!”, Celeste Kingston growled and dropped her phone back into her purse with an exasperated huff. “What a load of crap.”

“And yet you can't quit it”, her best friend Annie Montgomery gave back with a light chuckle. “You love it when they talk about you. Especially when they make up drama.”

She leaned back in her seat and looked out at the East Hamptons passing by the town car's tinted windows.

Being able to come here whenever she wanted had always been one of the few things she had unreservedly loved about moving to New York, but this time the picturesque houses and glittering coastline didn't have the same calming effect on her they usually had.

She was practically buzzing with anxiety – a strange, tingling sensation like ants crawling right under her skin, which grew worse with every passing minute. She had known that this moment would come eventually, that she couldn't run away forever, but now that they were almost there the thought alone was enough to make her feel nauseous.

“All publicity is good publicity”, Celeste stated. “Ever since the golden days of Blair Waldorf and Serena van der Woodsen no one has been proclaimed Queen of anything if Gossip Girl didn't find them worthy of... well, gossip. Speaking of which...”

She had been checking her reflection in a small hand mirror, fixing already flawless ginger beach waves – strawberry blonde, her hair colorist Hugh called it, heavy on the strawberry - but now she turned to Annie with a conspiratorial grin. “You know that you're gonna have to tell me who's been calling you all summer eventually, because that's what BFFs do. You might as well just get it over with and tell me right now.”

“I already told you it's nothing”, Annie replied weakly, not daring to look her best friend in the eyes as she lied to her again. She had repeated that same lie over and over for weeks now, but it still left a stale taste in her mouth. “Just some guy I met before we left. Turns out he was far more interested than I was, so I stopped answering his texts. I'm sure he'll stop calling eventually.”

“Next time he calls just give me the phone”, Celeste suggested with a shrug. “I'm sure I'd get the message across loud and clear.”

“I really don't think that's necessary”, Annie replied quickly. Maybe a little too quick, but thankfully Celeste could hardly go two minutes without getting distracted by her phone, so she was already too busy scrolling through her messages to notice.

“Right, whatever... Keep your stalker. Anyways, Maddie's still in Europe, but The twins are gonna meet us at Jack Bass's garden party”, she said in that tone that her boyfriend Quinn Davenport called her “that's an order, not a suggestion” voice, so Annie didn't even bother trying to tell her that all she wanted from this day was a long, hot shower and to hide away on her porch with a good book until it was time to go to bed. She would have been fine to spend the rest of the summer like that. But the Queen had spoken. Garden party it was.

Annie breathed a silent sigh of relief when they pulled up in front of her grandma's beach house. It was the Fourth of July so naturally traffic from the airport had been an absolute nightmare and Annie couldn't wait to finally get out of that car. In fact, she was so eager to get out that she didn't even wait for the driver to come open the door for her.

“Thank you so much for this, trip, Cee”, she really hoped that she managed to sound at least somewhat genuine. Taking her to the Caribbean for a month had been a very generous gift after all – even if the only reason Annie had come was that she hadn't been able to come up with a good enough excuse not to. And now she was glad it was over.

The past four weeks had been overall terrible for the both of them – and for each of them for very different reasons – but ever since they had gotten on Celeste's father's private jet about seven hours ago, Annie had been feeling downright claustrophobic. Like all the lies were weighing her down, making it harder and harder to breathe.

She was damn lucky that Celeste had her own problems to chew over. Otherwise she probably would have wondered what the hell had turned her low-maintenance best friend into such a train wreck all of a sudden.

“You should call Quinn when you get home”, she said as she took the bag and suitcase the driver handed her from the trunk, trying not to trip over the way it felt to even say his name. “Tell him before the story hits the tabloids, so he can be there for you when it does.”

“There is nothing to tell”, Celeste hissed, her mouth a tight, grim line. “This... thing will die before either of us can say 'National Enquirer'. And this is the last time you and I are ever gonna speak of this, do you understand me?”

Normally Annie didn't take well to Celeste talking to her like she was one of her Constance Billard underlings, but right now all she wanted was to go inside and finally be alone, so she decided to let that one go.

“Got it”, she said softly. “I didn't mean to upset you, Cee, I'm sorry. ”

“And I'm sorry I snapped at you.”

And as if it wasn't 'once in a blue moon' enough to hear Celeste apologize for anything, she then further surprised Annie by slipping out of the car and engulfing her in a tight hug.

"Thank you for being there for me", she whispered, her voice cracking ever so slightly. "I would've gone crazy without you..."

"Cee..." Annie had to blink back tears. There was so much she wanted to tell Celeste in this moment. How much she loved her. What their friendship meant to her. How badly she had fucked up... But she couldn't.

Because she didn't want to lose her. Because what she had done was unforgivable. Because saying the words out loud made it real.

She felt like this day's anxiety was very rapidly turning into a full fledged panic attack.

"I should get going", she said and took a step back. "I really need to wash off the travel smell and figure out what to wear tonight."

“Girl, same”, Celeste gave back with a shaky laugh and slid back into the backseat with enviable elegance. “Do you want us to come pick you up?”

“No, thanks.” Annie shook her head. The prospect of spending any amount of time in a confined space alone with both Celeste and Quinn was probably in the top five of things which for the past few weeks had kept her awake at night. “The Bass's house is just down the street. I think I'm gonna do something for my carbon footprint and walk.”

“Fine by me.” Celeste shrugged and motioned for the driver to close the door. “See you there then.”

Annie felt like a weight was being lifted off her shoulders when the black car was finally rolling down the driveway, but just when she was about to turn around and go inside, the rear window opened and Celeste's grinning face appeared.

“Just so you know, Gossip Girl's right!”, she called. “I'm not gonna share my prom date with you again. Put on something hot tonight, we're gonna find you a boyfriend!”

Luckily the car was already so far away that Celeste didn't see how her best friend blanched at her cheery little jab. Annie waved one last time and then the car was gone. She unlocked the front door, completely forgetting about her bags in her eagerness to get inside and then she was finally, _finally_ alone.

 

~*~

 

Annie quickly closed the door behind her, pressing her trembling hands flat against the cool, painted wood.

The house was completely silent save for the distant roll of wave outside, the ticking of the antique mahogany clock in the living room and her own ragged breathing.

She closed her eyes, trying to focus on the soothing sound of water lapping on sand and on her own breathing - in through the nose, tick tock, hold, tick tock, out through the mouth, tick tock - until she felt like she was no longer about to hyperventilate. She was still feeling miserable, but at least she wasn't in full on panic mode anymore.

Yes, she had gotten herself in an awful fucking mess, but she needed to keep a clear head if she wanted to find a way back out of it that didn't involve wrecking her own life and those of the people she cared about the most in the process.

" _A little late for that_ ", a nasty little voice in her head taunted. And it was right.

There had been plenty of moments when she could have stopped all this from happening - last month or back at prom and even a little bit on every single day of the past two years. But she hadn't. The damage was done and now that they'd spend the rest of the summer in the Hamptons together, it was only a matter of time before the truth would come out and leave her with nothing.

She had half a mind to just board the next bus into the city, spend the rest of the summer hiding in the Manhattan penthouse or maybe go and visit her grandparents in LA. It didn't even matter where she went as long as she didn't have to be _there_. With her bags still conveniently packed on the porch outside it was a tempting idea. _Very_ tempting.

But Annie knew that if she ran now, she would just be buying time. In September she would have to return to school and Constance Billard was a cesspool for gossip. After all it was the birthplace of Gossip Girl and very possibly the lair of 'Her' current incarnation.

There was no way her secret would stay hidden there. Shit would hit the fan eventually, only then she would have to deal with the fallout in front of all her classmates. Even a decade later there was still talk at Constance about the infamous ' _Blair Waldorf Pregnancy Scare of 2008_ ' and Nate Archibald decking Chuck Bass in the face in front of the school. Annie could live without any such public scene.

So running, while tempting, wasn't an option. Plus, her grandma's beach house was probably her favorite place in the world, where else was she gonna feel save enough to get this whole mess sorted?

“Grow a pair, Montgomery”, she muttered to herself.

She opened the front door to pick her bags from the porch before her _cowardly lion_ side reared its ugly head again and made her change her mind. Her grandma was spending the summer in Florida and her dad had gone back to the city two days ago for an urgent client meeting and wouldn't be back for at least a week, so for now she had the place to herself. That gave her plenty of time and room to figure things out in peace. If only she didn't have to go to this stupid party...

As if on cue, her phone buzzed softly in the back pocket of her jeans. She sighed. Probably Celeste with some party ' _emergency_ '. Annie took her phone out and looked at the screen. It felt like suddenly someone had knocked all air from her lungs. It was a message from Quinn.

 

**Quinn Davenport (2:25pm):** _We need to talk._

 

_Well, fuck._

She hastily put the phone back, as if this way she could just unsee the message. She had ignored Quinn's calls and texts for weeks, what difference did another day make? She wasn't ready to face him yet - would probably never really be ready again – but it seemed now that Gossip Girl had told the whole world she was back, he wasn't gonna let her ghost him like she had done for the past month.

Her phone buzzed again. And again. In the end Annie put her it in her bag which she left in the hallway. With Quinn just a quick walk along the beach away, instead of a five-hour flight she didn't trust herself not to cave if he messaged again or even worse, called her.

All she wanted to do now was unpack, maybe eat something and spend the next eight hours bracing herself for what was to come.  
Her grandma had spent the last two years and an obscene amount of money on the house getting both refurbish and modernized, so while the outside was still all rustic Hamptons charm, the inside was dominated by wide open spaces, white walls and beige upholstery.

When Annie entered the polished, open kitchen there was a freshly filled fruit bowl sitting on the counter. Upon a quick inspection she found that the kitchen cabinets too were well-stocked with the essentials. There was even milk and yogurt in the fridge. When she picked an apple from the bowl she found a note on the counter. She immediately recognized her father's handwriting.

 

“ _I had Katherine restock the kitchen for you. See you on the 13_ _th_ _. Love, Dad._

_PS: Your grandma can smell the remains of a party through three layers of bleach, so don't do anything I wouldn't do.”_

 

Annie smiled at the note. It was so like her dad to tell their housekeeper to prepare the house for her, even after she had told him he didn't need to. Sometimes she thought that for Declan Montgomery she would always be a twelve-year-old with braces who couldn't possibly take care of herself for a week. It was endearing. Annie had really missed him while she was away. She would definitely call him later.

She took her stuff and went to the living room. There she opened the massive glass sliding door which led into the back garden with access to the beach and stepped out onto the terrace.

The Garden was her grandmother's pride and joy – beautiful, old trees, meticulously trimmed hedges and rosebushes of all sizes and colors that filled the air with almost dizzying fragrance. The spacious lawn had seen a lot of rousing garden parties in its time.

Annie closed the glass door behind her. As much as she loved the house, she had no intention to be staying there, because her favorite spot was the little pool house at the far end of the garden. Even if in that case the ' _little_ ' house came with a separate bedroom, its very own kitchenette and a bathroom with a rain forest shower. Annie loved being able to take a quick dip in the pool without having to walk through the whole house and garden to get there. She loved using the outside shower on a hot day and she loved that the pool house was right next to the garden gate that led to her family's small strip of private beach – not that anyone in her family actually cared much about who used it so long as it was clean when they left.

It was a secret no one really tried to keep that sometimes – when her dad and grandmother weren't there, of course – the resident kids would have their beach parties on the Montgomery's property, as it was a lot nicer than most of the public beaches. And they always cleaned up before they left, because the last thing they wanted was to come back and find a brand new fence around their favorite hangout.

The key to the pool house was hidden under a fake stone by the door – not very creative, but with a high end security system there wasn't much need for creativity there. Annie unlocked the door and carried her stuff inside. She dropped her bags in the bedroom, then went and opened all windows to let the fresh smell of sea breeze in. The tidy side of her thought she should probably unpack, but the restless, anxiety ridden main part of her just wanted to get in the pool and do laps until her body screamed and her mind went blank.

So she did just that. She slipped into her favorite pastel striped Farrah swimsuit, grabbed a towel from the bathroom and went outside. She quickly showered – the past eight hours weren't something she was keen on carrying into the water with her – then took the steps by the narrow end to get into the pool.

When the pool and pool house had gotten their big make-over last year, the pool had been tiled in a very expensive, very intricate mosaic that shimmered in various shades of green, blue and purple and as Annie glided through the water as fast as she could, it felt like she was surrounded by countless glistening mermaid fins. It was a mesmerizing illusion and soon Annie was so lost in the fantasy it conjured that at least for one moment she was able to put her worries on mute. She didn't stop until her lungs were burning and her arms felt like lead. The last thing she expected when she came up, gasping for air was to find Quinn Davenport standing at the pool edge, watching her.

“That was impressive”, he said with that stupid soft smile that had never failed to make her weak in the knees ever since she had first met him right there in the Hamptons five summers ago. And even now, despite everything that had happened, the mere sight of him and that _stupid_ smile was enough to make her _stupid_ heart skip a beat. “Are you planning on trying out for the swim team this year?”

He could've fooled her with that smile and the light tone to his voice, but she knew him too well. His eyes gave him away. Always his eyes. To Annie, Quinn was the worst liar in the world and it was all in his eyes. She asked herself if Celeste knew that, too.

“What are you doing here?”, she asked, her tone sharper than she had intended to, as she hastily scrambled out of the water and grabbed her towel from a sunbed. She quickly covered herself with it, even though she knew it was silly. _Nothing there he hasn't seen before, idiot._

But she wasn't going to be doing... _this_ standing there in nothing but a dripping wet swimsuit while he looked like a walking billboard with his blue chino shorts and light gray polo shirt. His hair was a charmingly windswept mess and the sun had turned his usually caramel brown waves an almost honey blonde shade. He had the natural tan of someone who spent all day every day at the beach and even from where she was standing, Annie could see the freckles on his face and arms.

“Well, I figured it'd be much harder for you to pretend like I don't exist if I came here instead of sending you another text”, he gave back dryly. Annie felt like she probably deserved that one. “I knocked at the front door, but when no one answered I figured you were probably out here or in the pool house and I still have the code for the garden gate so...”

He trailed off and took a few tentative steps towards her, but stopped, when he saw her moving back ever so slightly. He looked at her, brows furrowed. There was no mistaking the fact that he was hurt. Annie opened her mouth to say something, then closed it again. She sighed. _What a fucking mess._

“You cut your hair”, he said, breaking the uncomfortable silence between them. “I like it.”

“I felt like a change”, she mumbled, one hand unconsciously reaching for a strand of wet, chin-length hair. It had been a spur-of-the-moment thing, back in St. Barts when she had felt like crawling out of her own skin. Celeste had dragged her to her favorite spa on their third day there. It had been the usual – mani-pedis, facials and massages, but while Celeste had finished her day by getting a professional blow-out, Annie had ended up getting almost ten inches of hair chopped off.

“ _You know_ ”, Celeste had quipped while inspecting her best friend's brand new feathered bob. “ _If I didn't know better, I'd say someone's getting over a bad break-up_.” Of course Annie had laughed it off, but her stomach had churned with guilt.

“You shouldn't have come here”, Annie said, the thought of Celeste enough for her to stop beating around the bush. She needed to end this before Quinn had a chance to say what he had come to say. He was looking at her in that way again. The way that made her heart flutter, the one that made his hazel eyes crinkle softly at the corners. She remembered the times she had caught herself wishing he'd be looking at _her_ like that, but now all it did was fuel the feeling of guilt she had been carrying around with her over the past weeks. “I know you think we need to talk about... about what happened. But we don't.”

“Of course we do.” For a moment it looked like Quinn was going to step towards her again, but he didn't. Annie knew that it was probably because of how she had recoiled from him earlier and she couldn't fight the pang of regret. She had never met anyone who was so _aware_ of the way their physical appearance affected others.

Standing at 6'3 with the broad shoulders of a competitive swimmer, Quinn knew he was intimidating to people who didn't know that somewhere deep down he still felt like the lanky thirteen-year-old boy whose limbs never really seemed to fit in with the rest of his body.

The last thing Annie wanted was for him to think that she could ever feel threatened by him. But she couldn't tell him that the thing that actually frightened her was the way she was feeling whenever he was close to her.

“Please, Annie”, he begged softly. “We can't just pretend like nothing happened.”

“I can't do this right now”, she shook her head. All she wanted was for him to leave, so this fog around her brain would lift and allow her to think clearly again. She almost laughed at her own stupidity. Apparently now she was also lying to herself. She hadn't been thinking clearly in four weeks, three days and fifteen hours. But Quinn had completely blindsided her by turning up at the house like that and now she felt cornered. Trapped. This was not at all going the way she had pictured it – the _very few_ times she had actually allowed herself to even think that far. “I need more time...”

“ _More time_? Annie, you've been gone for over a month. You didn't take any of my calls or answer any of my texts. How much more time could you possibly need?” There was an urgency in his eyes – a passion – that made Annie's inside hurt with longing. If only the circumstances were different, maybe they could – “Cee's called me two times already. She wants to see me. We need to talk about what we're gonna tell her.”

_Cee_. The sound of her best friend's nickname brought reality crashing back in with a bang and the old panic right along with it.

“There's nothing to tell”, she croaked. “She's probably waiting for you to call her back. You should leave.”

“Annie...”, he pleaded. He moved, raising his hand as if he wanted to touch her and for a brief moment every last piece of her begged her to just _let him_. But she couldn't do that. It wouldn't have been fair to him. To herself. To _Celeste_.

“I told you to _leave_!”, she cried, her voice breaking on something close to a sob. “Please, Quinn!”

Annie didn't know what ultimately did it – was it the tears brimming in her eyes or was it the fact that she was practically radiating despair at this point? - but it was like whatever hope or confidence this whole confrontation had left him with had just been drained from his body. He looked younger suddenly, and just as vulnerable and hurt as she was.

“Okay”, Quinn said bleakly. “I’ll see you at the party.”

Then he turned around and left, his whole posture a picture of defeat. He didn't look back at her once. And Annie found herself frozen in place, still staring at the garden gate long after it had fallen close behind him.

She faintly noticed that she was shaking so hard her teeth rattled and realized she was still standing there in nothing but a wet swimsuit. She quickly went inside, stripping down and stepping inside the shower. She stayed there until the hot water ran out, then toweled herself off, slid into a soft, off-white dressing gown and went into the bedroom to unpack. All of this she did in a kind of misty haze where she was replaying the past minutes in her head over and over again until she wasn't even sure anymore if it had actually happened the way she remembered it or not.

When Annie was done the dated alarm clock on the nightstand told her that she still had at least four hours left before she had to get ready for the party. And even though she wasn't too keen on going – for obvious reasons – she felt like she was going to go crazy sitting around with nothing to keep her mind from wandering. She grabbed her purse from the bed to get her phone. She would call her father, maybe he would be able to comfort her, even though she couldn't really tell him what was going on with her either. Annie loved her father, she really did, but there were certain aspects of her life that she rather not share with him in too colorful detail.

She sighed when she saw the flood of new messages on her phone. There were at least six texts from Celeste – all of them pictures of her in various party outfits. Where the hell had she gotten a 'Stars and Stripes' sequin dress? Annie could've sworn she didn't have it with her when they had packed last night. Maddie had sent a picture of herself in front of the Eiffel Tower in their group chat that Celeste had aptly named “Constance Royal Court” after Rachel Cavalli had crowned her new Queen B at the end of their sophomore year. Then there were the three messages Quinn had sent her earlier and that she had ignored.

 

**Quinn Davenport (2:25pm):** _We need to talk._

**Quinn Davenport (2:25pm):** _Please._

**Quinn Davenport (2:26pm):** _I'm coming over._

 

Looking back now, she probably should have read those texts. There was another message from him. It was a voicemail, dated 3:47pm. He must've sent it right after he had left. Her finger hovered over the message, unsure if she even wanted to hear it. What more was there left to say? She took a shaky breath and hit 'play'.

 

“ _Hey... You probably won't even listen to this, but I- I don't know... I guess I just wanna apologize. For showing up at your place like this. For trying to make you talk even though you said you weren't ready. But the thing is, Annie, I am ready to talk about this. I have been ready to talk about this for over a month now. And I know you feel guilty, Annie. I'm feeling guilty, too. But we can't just ignore what happened. Annie, we slept together and all the silence in the world isn't going to undo that...”_

 

_~*~_

 

 

 


	2. pt.2

**Summary for the Chapter:**

> “Drink up”, she ordered. “You look like you're about to have your wisdom teeth removed.”  
> “This sounds like an attractive alternative right about now”, Annie muttered, downing the whole drink in one angry gulp as she followed Celeste outside.

_~*~_

  


About six hours later Annie found herself walking up the sweeping, graveled cul-de-sac to the Bass's massive villa. She had taken the 'scenic' route along the beach, but when she had arrived at the double iron gate that separated the estate from the beach, a security guard approximately the size of a tree had stopped her.

“Entry only through front door”, he had said sternly, his thick accent placing him somewhere in the East of Europe. “But is invite only.”

“That won't be a problem”, she had replied with a polite smile. Her dad had left her the invite on the living room table with a little note that told her he'd RSVPed on her behalf. _Just in case_. “Thank you.”

There was a public walkway that led back to the street, but it was at least a quarter of a mile down the beach and an even longer walk back up the street to the house, so instead Annie turned to an overgrown dirt track between the Bass's hedge and their neighbors' fence.

It was a popular shortcut and every time either of the two adjacent owners had tried to close it some way or the other they had come back in the summer to find it back in business until they had given up. Rumor had it they were now in talks with the town council about having it paved and turned 'official' – all in the name of giving back to the community, of course. No better way to do good than by giving away something that's no use to you anyways.

When Annie had lived in Beverly Hills most parties she'd been to had been loud music, crowded dance floors and flashing strobe lights – even those that had been held by friends of her parents – maybe a by-product of living in the heart of La La Land. But Manhattanites were different; sophisticated to a fault and very proud of it. Ever since Annie and her dad had moved to live with her grandma on the Upper East Side it had been an endless cycle of chandeliers, champagne and what could only be described as overpriced elevator music. The first time Annie had chucked a red cup at an NYU frat party in front of Cee, her best friend had looked at her like she had just grown a second head.

Annie had silently hoped a Fourth of July bash arranged by none other than the notorious Georgina Sparks – aka. the soon-to-be Mrs. Jack Bass – would be a breath of fresh air, but when she walked up the semicircular staircase leading up to the entrance she felt those hopes being crushed by a glow of dimmed lights in the windows and the discreet sound of a piano being carried through the open front door. Looked like Ms. Sparks had already well adjusted to her future role as a _Real Housewife of Manhattan_.

Celeste ambushed her in the foyer.

Annie had barely had time to put the invite back into her Cashhimi clutch when her best friend came towards her with a half empty champagne flute in her hand and purpose in her steps.

For one foolish second Annie panicked. Had Quinn told her? Did she know? But her face didn't say _murder_ , so whatever was driving her right then, it wasn't a hunger for blood.

"You're late", she said. No hello, no nothing. Classic Cee. "I was starting to think you were standing us up."

"I wouldn't dream of it", Annie gave back with a grimace. "Besides, I am still well within the fashionable two hour range. If anything _you_ are too early."

"Touché." Celeste raised her glass and stuck out her tongue at her. "I went four weeks without a proper Upper East Side party, so I wanted to make the most of it."

Annie thought about how she would have preferred to spend the evening alone with her Netflix account and pizza delivery instead. In her head she was already contemplating how long she would have to stay until she could leave. Cee linked arms with Annie, pulling her along through the living room and towards the open terrace door.

“You know, Georgina Sparks will probably call security on your ass, if she catches you in _those_ ”, she commented, with a pointed look at Annie's black espadrille wedges. “What happened to our “ _No Heels no Party_ ” rule?”

“You mean _your_ “No Heels no Party” rule”, Annie gave back dryly. “I wasn't gonna do a twenty minute walk along the beach in heels, Ms. Fashion Police. Besides, I've seen our host. She looks like she is about twenty months pregnant and probably wishes she was wearing flats.”

“She does look _very_ pregnant”, Celeste agreed with a grin. “That's no excuse to show up at a Hamptons party in shoes with ropes for a sole though. You're lucky the guy I found for you thinks this is the kind of event that calls for a canvas shirt. You two are ridiculously perfect for each other.”

“Wowowowow, wait!” Annie came to an abrupt halt, yanking hard enough at Celeste's arm that she tripped and spilled a bit of champagne on the dress of a middle aged woman with hair that was a little too yellow and a forehead that was a little too smooth.

“What do you mean _the guy you found for me_?”, she hissed, flashing the woman an apologetic look, before turning her attention back to her best friend. “Please tell me that I am not about to be set up with some random dude.”

“Oh don't worry, he's far from random”, Celeste answered suggestively. “His questionable fashion sense aside, he's actually gorgeous. Type _tall, dark and handsome_ and built like a tree. If I wasn't happily otherwise engaged, I'd probably keep him for myself. _And_ he just recently moved here from California. It's like he's been sent here specifically to end your little dating dry spell.”

“I'm not having a dry spell!” Annie felt a heat rising in her cheeks that was equal parts anger and embarrassment. And shame. “And I don't need to be set up with a guy I've never seen before in my life.”

“How about you wait and see before you decide?”, Celeste offered, completely unfazed by her friend's irritation. “He's outside with Quinn and the twins. You're gonna meet him either way, so you might as well give him a chance.”

“Fine”, Annie growled. “Does this guy have a name?”

“Of course he does”, Celeste quipped. “I think it was Jack. Or Jim? Pretty sure it was something starting with J... To be honest I've been too distracted by his abs under that ridiculous shirt to really listen.”

She stopped a waiter on his way into the house and swapped her empty glass for two full glasses from his tray, handing one to Annie.

“Drink up”, she ordered. “You look like you're about to have your wisdom teeth removed.”

“This sounds like an attractive alternative right about now”, Annie muttered, downing the whole drink in one angry gulp as she followed Celeste outside.

Their friends were standing at the champagne bar that had been set up by the illuminated swimming pool. Annie found her eyes immediately drawn to Quinn. He looked unbelievably handsome in his white button-down shirt and cream colored pants that Celeste had one hundred percent picked out for him and she felt her heart ache in the exact same way it had whenever she'd seen him for the past two years. Funny, how the more things changed the more they stayed the same.

How stupid of her to think – hope even! – that anything remotely good could come from that ugly, fucked up mess she'd made. That maybe by acting on those fantasies she had tried so hard to bury, she had finally gotten Quinn out of her system. But like with so many other things lately she had been dead wrong.

Now she'd had a glimpse of what it was like to be with him – seeing him that afternoon and even more so seeing him now – suddenly it felt like all she could think about was _how much_ she longed to be with him like that again. This feeling – this desire – was so powerful, so consuming that for a moment Annie forgot everything else. Like the whole world had been turned into a blur until all she could see clearly was him.

Reality came crushing back in swiftly and in the form of Sophia and Nicky Redford, aka. “The Redford Twins”, who'd erupted into excited cheers when they had seen her step onto the terrace. And for a short while everything was hugs and cheek kisses and happy chatter that was lost in the overall joy of the moment.

Annie adored the twins. In fact, she had already admired them from afar since before they had met at Constance two years ago. They were exceptionally clever and beautiful and just overall interesting young women. Starting with, but not limited to the fact that they weren't actually twins. Technically, they weren't even related. A black girl and a Latina girl growing up as sisters on the Upper East Side following the wedding of their parents twelve years ago. They had been as thick as thieves from the moment they met. And they had quickly learned how to cash in on the fact that they were a small Manhattan sensation.

There had been a time when their blog had attracted almost as much traffic as Gossip Girl. Especially after the “St. Mary's Science Fair Incident”, when they had collaborated on a project called “Things I'll get away with doing (that my black Sister won't)”. There's never been a complete version of said project anywhere on the internet and witness reports largely differed on the number and severity of the incidents listed in the twins' paper, but it had been enough to have the private middle school issue an official apology on their website and on a local news segment.

Last year Nicky had decided to very publicly come out as bisexual - "I can do it now or I can wait for that Gossip Bitch to do it for me", she had told Annie with a shrug - and when Richard van Stroup III – a disgusting little lacrosse jock whose father was a full time property shark, slash slumlord and part time Trump suppository – had kept harassing her between classes, making obscene gestures and suggestive remarks about the sisters “sharing a bed”, Sophie had punched him so hard in the face she had broken his nose in two places.

She had faced the possibility of being expelled for assaulting a fellow classmate, but luckily it had become very clear which tree the combative apple must have fallen off the second Nicky's mother had stormed into the school, a vision of patchouli, paint spots and righteous fury.

In the end Sophia was still in school with not even the tiniest entry in her file while Richard's father was still desperately trying to find a college that needed a new building and was willing to take his cockroach of a son after he had been forced to transfer to a boarding school in Long Island.

Long story short, the twins were badass and Annie had no idea why they had decided to settle for life in the shadow of “Queen Celeste” when they could have single-handedly won over Constance had they set their mind to it.

“This is great”, Celeste beamed. “The whole _Court_ finally together again.”

“Maddie's not here”, Annie corrected her almost automatically. For as long as she'd been a part of the group, Madeleine Hayes had never made it past being a sort of afterthought for Celeste. Sure, she was pretty and she was clever, but so was almost every single girl at Constance Billard. Annie was positive that her best friend wouldn't have looked at the younger girl twice, had she not gone through a very becoming “growth spurt” right before her sophomore year, awarding her the questionable nickname “Makeover Maddie”.

There was rumors that it hadn't been just nature that had its hand in Maddie's transformation from duckling to swan. Annie was pretty certain that Celeste had started some of those rumors, if not all of them.

“Yeah, I know”, Celeste said, waving her off with the same bored gesture she would use to get rid of a mildly annoying fly. “I'm gonna text her later. But first let me introduce you to our new friend...” She trailed off, looking around with brows furrowed. “Where's _Tall, Dark and Handsome_?”

“Getting drinks.” Sophie nudged Annie's shoulder with a broad grin. “You're such a lucky girl. Tyler is pure eye candy. I would totally wanna tap that, but Cee has made it very clear that he's off limits.”

“ _Tyler_ , huh?”, Annie chuckled. She opened her mouth to mercilessly tease Celeste for the whole 'something starting with J' bit, but then she caught Quinn looking at her and the words got stuck in her throat. He looked... miserable. Like the mere thought of her meeting another guy was unbearable. It felt like someone had put the world in slow motion as they stood there, surrounded by their friends, staring at each other like idiots. How could he just look at her like this? Right there in front of everybody. In front of Celeste. How was she not supposed to notice what was going on right under her nose?

“Did I hear someone say my name?”

And suddenly there was Mystery Guy, balancing a full tray of champagne, breaking the tension and thus very possibly saving the day. Even in her Quinn-induced haze Annie had to admit that both Celeste and Sophie had been spot on. Tyler was _spectacular_. Tall, dark and handsome indeed.

He was at least 6'4, but maybe he was looking even bigger than he was, because when Celeste had told her he was built like a tree she had not exaggerated. Neither had she been lying about his abs showing through the thin fabric of his shirt - which might not have been the perfect fit for the occasion but together with a pair of dark washed jeans made for a great outfit. He had dark eyes and straight, black hair that almost reached to his chin. In short, Annie had no idea why Celeste was under the impression he could possibly ever be interested in her.

“I hope it was something nice”, he joked as he casually passed each of them a glass of champagne.

“Actually, I was just telling my friend here about you”, Celeste answered with that special, saccharine smile she usually reserved for teachers and connected Ivy League alumni only. “That's Annie. She's from LA, too.”

“Nice to meet you, Annie.” He offered her his hand with a smile.“Where did you live? Maybe we've run into each other somewhere."

“I think I would remember if I had bumped into someone like you”, Annie was equal parts surprised and mortified at how easy the playful remark had come to her. Even out of the corner of her eye she could tell that Celeste was practically buzzing with excitement and Qinn was... not. “I lived in Beverly Hills.”

“Then we probably didn't meet”, he laughed. “I moved here from Glendale. I have a feeling we didn't exactly move in the same circles.”

Annie didn't know how to respond to that. She had become so used to looking down her nose when it came to the Upper East Side and its unparalleled elitism, she had completely forgotten that in LA there had been places too that might as well have been on a different planet instead of a mere one hour drive outside Beverly Hills.

Tyler looked at her, politely waiting for her to say something. Like any normal person would in a friendly round of small talk. But Annie wasn't the smoothest small talker even on her best days and this definitely wasn't one of her best days. The playfulness she had somehow unexpectedly displayed just moments ago had practically drained from her. Instead she found that right then and there – trapped between her best friend, a handsome stranger and the boy she'd been in love with since she was thirteen years old – her conversational skills had basically been stripped down to nonexistent.

“And yet you're both here now”, Celeste chimed in when the silence between them threatened to move from awkward to uncomfortable territory. “I'd say it's fate.”

“I'd say it was the charming young lady who came up to me, felt up my arms and asked me if I wanted to meet her hot, single friend”, Tyler gave back good naturedly. “Definitely didn't see that coming.”

“Oh my god...”, Annie mumbled, covering her face with her hands to hide her embarrassment. “Cee...!”

When she looked back up the twins were pointedly avoiding her eyes and Celeste seemed... weirdly happy with herself and completely oblivious to her discomfort.

“Come on, Annie. I told you I'd find you a guy. And not to butter my own parsnip here, but I think I delivered.”

“I'm just gonna go and take that as a compliment”, Tyler offered with a careful smile, obviously catching up on the sudden change of tune around him and trying to lighten the mood. It didn't work.

Annie couldn't think of another time when she had felt more humiliated than she was feeling in that exact moment. It didn't help that she could still feel Quinn's eyes positively boring into her. She looked at him and could tell immediately that he was physically struggling to keep his mouth shut. Suddenly Annie felt like she was gonna throw up and all she wanted was to get out of there as fast as she could.

She was distantly aware that her phone buzzed softly in her clutch. Just once, probably because of a message or an email, but it gave her an idea.

“That's my phone”, she told the others in an unexpected moment of inspiration, vaguely gesturing at the small bag, pretending her phone was still buzzing inside it. “I told my dad he could call me tonight and... I'll just be a minute.”

And with that she bolted, handing her glass of champagne back to Tyler with an apologetic little smile and then practically making a beeline for the house. She needed to get out of there. Not just out of this house and away from this party. In that moment all Annie wanted was to get out of the Hamptons, out of Manhattan and away from the Upper East Side. For the very first time she understood what had driven Serena van der Woodsen out of the city all those years ago.

Annie quickly made her way through the living room, not caring anymore if she knocked into people. She didn't care if Celeste and the others would be mad at her for bailing on them like that. That was a problem for tomorrow's Annie. Today's Annie just wanted to go home, crawl into bed and cry herself to sleep.

There was an antique dressing table nested in a small alcove in the hall and as she hurried past she caught a glimpse of herself in the old mirror – wide eyes in a pale face, framed in mahogany.

“Annie, please!”

She had almost made it to the door when the sound of Quinn's voice stopped her. She turned around to find him standing just a few feet away from her with a pleading look on his face. He was out of breath and visibly shaking.

“I'm going to break up with Celeste.”

  


~*~

 


End file.
